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Highly Controlled Molecular Conversion by Radical Species

Research Project

Project/Area Number 26248031
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

Ryu Ilhyong  大阪府立大学, 研究推進機構, 特認教授 (80210821)

Co-Investigator(Kenkyū-buntansha) 福山 高英  大阪府立大学, 理学(系)研究科(研究院), 准教授 (60332962)
植田 光洋  大阪府立大学, 理学(系)研究科(研究院), 講師 (60566298)
Project Period (FY) 2014-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥41,990,000 (Direct Cost: ¥32,300,000、Indirect Cost: ¥9,690,000)
Fiscal Year 2018: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2017: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2016: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2015: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2014: ¥15,470,000 (Direct Cost: ¥11,900,000、Indirect Cost: ¥3,570,000)
Keywords位置選択的反応 / C―H官能基化 / 光触媒 / ラジカル極性効果 / ラジカル立体効果 / 高熱反応 / 一電子移動 / 無触媒カルボニル化 / ラジカル反応 / 水素引き抜き反応 / カルボニル化反応 / Minisci反応 / アルケニル化反応 / アリル化反応 / 硫酸ラジカルイオン / 位置選択的CH開裂 / CH/CC変換 / 電子移動 / C-H結合活性化 / デカタングステートイオン / パラジウム / ラジカル / 極性効果 / C-H開裂 / 光照射 / ポリオキソタングステート / Giese型反応 / 制御重合 / 位置選択的 / C-H官能基化 / アリル化 / ビニル化 / アルキル化 / カルボニル化 / ポリオキソデカタングステート
Outline of Final Research Achievements

Site-selective C(sp3-H) functionalization of was studied by radical reactions. Allylation of alkanes by allylic bromides proceeds site-selectivity at methine C-H bonds, in which bromine radical undergoes site-selective SH2 reaction. When decatungstate anion was used as a photocatalyst, the synergistic control of the SH2 transition states of hydrogen abstraction by polar and steric effects was effectively attained, providing a strategy in achieving site-selective C(sp3)-H functionalization. By using this approach, the C-H bonds of alkanes, alcohols, ethers, ketones, amides, esters, nitriles, and pyridylalkanes were functionalized site-selectively. Under photo irradiation conditions, alkyl radicals and aryl radicals were generated from the corresponding alkyl and aryl halides and thus generated radicals were subjected to C-C-bond forming reactions and reduction.

Academic Significance and Societal Importance of the Research Achievements

C-H結合の開裂はラジカル種により生起するが、その位置選択的な制御は一般に困難とされてきた。実際Barton反応に代表されるエントロピー制御による分子内反応の研究が多く行われている。本研究ではデカタングステートイオンを光触媒とする反応系で、位置選択的なC-H結合開裂反応を見出した。その結果、新しいC-H/C-C変換反応が開発され、ラジカル反応の潜在力に世界の注目を集める契機を与えた。本研究ではラジカル種の発生に光照射や高温加熱系を積極的に活用し研究を進めた結果、ハロゲン化アルキルからのアルキルラジカルの発生やハロゲン化アリールからのアリールラジカルの発生に成功し新しい有機合成方法論を提出した。

Report

(6 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report

Research Products

(89 results)

All 2019 2018 2017 2016 2015 2014 Other

All Int'l Joint Research (3 results) Journal Article (45 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 45 results,  Open Access: 15 results,  Acknowledgement Compliant: 26 results) Presentation (40 results) (of which Int'l Joint Research: 20 results,  Invited: 21 results) Book (1 results)

  • [Int'l Joint Research] Sorbonne University(フランス)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] National Chiao Tung University, Taiwan(その他の国・地域)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] University of Pavia(Italy)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis2019

    • Author(s)
      Cartier, A.; Levernier, E.; Corce, V.; Fukuyama, T.; Dhimane, A.-L.; Ollivier, C.; Ryu, I,; Fensterbank, L.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Pages: 1789-1793

    • DOI

      10.1002/anie.201811858

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Electron transfer-induced reduction of organic halides with amines2018

    • Author(s)
      Fukuyama, T.; Fujita, Y.; Miyoshi, H.; Ryu, I. Kao, S.-C.; Wu, Y.-K.
    • Journal Title

      Chem. Commun.

      Volume: 54 Pages: 5582-5585

    • DOI

      10.1039/c8cc02445f

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams2018

    • Author(s)
      Fukuyama, T.; Bando, T.; Ryu, I.
    • Journal Title

      Synthesis

      Volume: 50 Pages: 3015-3021

    • DOI

      10.1055/s-0037-1609964

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Applications of Radical Carbonylation and Amine Addition Chemistry: 1,4-Hydrogen Transfer of 1-Hydroxylallyl Radicals2018

    • Author(s)
      Matsubara, H.; Kawamoto, T.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Acc. Chem. Res.

      Volume: 51 Pages: 2023-2035

    • DOI

      10.1021/acs.accounts.8b00278

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes2018

    • Author(s)
      Fukuyama, T.; Sugimori, T.; Ryu, I
    • Journal Title

      Org. Biomol. Chem.

      Volume: 16 Pages: 7583-7587

    • DOI

      10.1039/c8ob01453a

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Theoretical Study on Radical-based Aminocarbonylation of Aryl Iodides2018

    • Author(s)
      Kawamoto, T.; Matsubara, H.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 9 Pages: 1169-1171

    • DOI

      10.1246/cl.180599

    • NAID

      130007472138

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Theoretical Calculations for the 1,4-Hydrogen Shift of 1-Hydroxyallyl Radicals Leading to α-Keto Radicals; Prediction of Facilitation by 1-Amino and 3-Tin Substituents2018

    • Author(s)
      Matsubara, H.; Kawamoto, T.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 9 Pages: 1197-1199

    • DOI

      10.1246/cl.180522

    • NAID

      130007472130

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Site-Selective C-H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope2018

    • Author(s)
      D. Ravelli, M. Fagnoni, T. Fukuyama, T. Nishikawa, I. Ryu
    • Journal Title

      ACS Catal

      Volume: 8 Pages: 701-713

    • DOI

      10.1021/acscatal.7b03354

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Site-selectivity in TBADT-photocatalyzed C(sp<sup>3</sup>)–H Functionalization of Saturated Alcohols and Alkanes2018

    • Author(s)
      T. Fukuyama, K. Yamada, T. Nishikawa, D. Ravelli, M. Fagnoni, I. Ryu,
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 2 Pages: 207-209

    • DOI

      10.1246/cl.171068

    • NAID

      130006337776

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium/Light Induced Radical Alkenylation and Allylation of Alkyl Iodides Using Alkenyl and Allylic Sulfones2018

    • Author(s)
      Shuhei Sumino, Misae Uno, Hsin-Ju Huang, Yen-Ku Wu, and Ilhyong Ryu
    • Journal Title

      Org. Lett.

      Volume: 20 Pages: 1078-1081

    • DOI

      10.1021/acs.orglett.7b04050

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photocatalyzed Site-Selective C(sp3)-H Functionalization of Alkylpyridines at Non-Benzylic Positions,2017

    • Author(s)
      T. Fukuyama,, T. Nishikawa, K. Yamada, D. Ravelli, M. Fagnoni, I. Ryu,
    • Journal Title

      Org. Lett.

      Volume: 19 Pages: 6436-6439

    • DOI

      10.1021/acs.orglett.7b03339

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Scalable Flow Synthesis of [6,6]-Phenyl-C61-Butyric Acid Methyl Ester (PCBM) using a Flow Photoreactor with a Sodium Lamp2017

    • Author(s)
      Ueda, M.; Imai, N.; Yoshida, S.; *Yasuda, H.; *Fukuyama, T.; Ryu, I.
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2017 Pages: 6483-6485

    • DOI

      10.1002/ejoc.201700745

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of -Bromoalkyl Radicals2017

    • Author(s)
      Kippo, T.; Hamaoka, K.; Ueda, M.; Fukuyama, T.; Ryu. I.
    • Journal Title

      Org. Lett.

      Volume: 19 Pages: 5189-5200

    • DOI

      10.1021/acs.orglett.7b02471

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ammonium Chiral Borate Salt Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with ,-Disubstituted Enals2017

    • Author(s)
      Ueda, M.; Yagyu, Y.; Ryu, I.
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 28 Pages: 1070-1077

    • DOI

      10.1016/j.tetasy.2017.06.003

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Flow Fischer Esterification of Carboxylic Acids with Alcohols Using Sulfonic Acid-Functionalized Silica as Supported Catalyst2017

    • Author(s)
      Furuta, A.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 90 Issue: 5 Pages: 607-612

    • DOI

      10.1246/bcsj.20170025

    • NAID

      130006770707

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Bromine-Radical-Mediated Synthesis of -Functionalized ,- and ,-Unsaturated Ketones via C-H Functionalization of Aldehydes2017

    • Author(s)
      Kippo, T.; Kimura, Y.; Ueda, M.; Fukuyama, T.; Ryu, I
    • Journal Title

      Synlett

      Volume: 28 Pages: 1733-1737

    • DOI

      10.1055/s-0036-1588494

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Regioselective [3+2] Annulation of ortho-Formyl and Acetyl Substituted Phenylboronic Acids with Alkynes2017

    • Author(s)
      Ueda, M.; Ueno, T.; Suyama, Y.; Ryu, I.
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Pages: 2972-2974

    • DOI

      10.1016/j.tetlet.2017.06.049

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ionic Liquids Are not Innocent in Pd Catalysis. C-H Arylation of Thiazolium and Imidazolium Ionic Liquids with Aryl Halides,2017

    • Author(s)
      T. Fukuyama, M. T. Rahman, H. Mashima, H. Takahashi, I. Ryu,
    • Journal Title

      Org. Chem. Front

      Volume: 4 Pages: 1863-1866

    • DOI

      10.1039/c7qo00331e

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cooperative Polar/Steric Strategy in Achieving Site-Selective Photocatalyzed C(sp3)-H Functionalization2017

    • Author(s)
      Keiichi Yamada, Takahide Fukuyama, Saki Fujii, Davide Ravelli, Maurizio Fagnoni, Ilhyong Ryu
    • Journal Title

      ChemEurJ

      Volume: 23 Pages: 8615-8618

    • DOI

      10.1002/chem.201701865

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoredox-Catalyzed Hydrodifluoroalkylation of Alkenes Using Difluorohaloalkyl Compounds and a Hantzsch Ester2017

    • Author(s)
      S, Sumino, M. Uno, T. Fukuyama,, I. Ryu, M. Matsuura, A.Yamamoto, Y. Kishikawa,
    • Journal Title

      J. Org. Chem

      Volume: 82 Pages: 5469-5474

    • DOI

      10.1021/acs.joc.7b00609

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane2017

    • Author(s)
      Furuta, A.; Hirobe, Y.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Pages: 1365-1368

    • DOI

      10.1002/ejoc.201700072

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis2017

    • Author(s)
      Wuattrini, M. C.; Fujii, S.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I.
    • Journal Title

      Chem. Commun.

      Volume: 53 Pages: 2335-2338

    • DOI

      10.1039/c6cc09725a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Palladium/Light System Combined with Hanztsch Ester: Radical Vinylation of Alkyl Iodides with Vinyl Bromides2017

    • Author(s)
      Sumino, S., *Ryu, I.
    • Journal Title

      Asian J. Org. Chem.

      Volume: 6 Pages: 410-413

    • DOI

      10.1002/ajoc.201600547

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Formal Total Synthesis of l-Ossamine via Decarboxylative Functionalization Using Visible-Light-Mediated Photoredox Catalysis in a Flow System2017

    • Author(s)
      Inuki, S.; Sato, K.; Fukuyama, T.; Ryu, I.; Fujimoto, Y.
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Pages: 1248-1253

    • DOI

      10.1021/acs.joc.6b02531

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of omethoxycarbonylphenylboronic acid with alkynes2016

    • Author(s)
      *Ueda, M., Ueno, T., Suyama, Y., Ryu, I.
    • Journal Title

      Chem. Commun.

      Volume: 52(90) Pages: 13237-13240

    • DOI

      10.1039/c6cc08032d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regio- and stereo-selective intermolecular [2+2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes2016

    • Author(s)
      Mitsuhiro Ueda, Tsukasa Sakaguchi, Miho Hayama, Takafumi Nakagawa, Yutaka Matsuo, Aiko Munechika, Shunsuke Yoshida, Hiroshi Yasuda, Ilhyong Ryu
    • Journal Title

      Chem. Commun.

      Volume: 52 Pages: 13175-13178

    • DOI

      10.1039/c6cc07320d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Flow Update for a Cossy Photocyclization2016

    • Author(s)
      Fukuyama, T.; Fujita, Y.; Rashid, M. A.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 18 Pages: 5444-5446

    • DOI

      10.1021/acs.orglett.6b02727

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A greener process for flow C-H chlorination of cyclic alkanes using in situ generation and on-site consumption of chlorine gas2016

    • Author(s)
      Fukuyama, T.; Tokizane, M.; Matsui, A.; Ryu, I.
    • Journal Title

      React. Chem. Eng.

      Volume: 1 Pages: 613-615

    • DOI

      10.1039/c6re00159a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes2016

    • Author(s)
      *Ueda, M., Nakakoji, D., Kuwahara, Y., Nishimura, K., Ryu, I.
    • Journal Title

      Tetrahedron Lett.

      Volume: 57(37) Pages: 4142-4144

    • DOI

      10.1016/j.tetlet.2016.07.089

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes2016

    • Author(s)
      Kippo, T., Hamaoka, K., Ueda, M., Fukuyama, T., *Ryu, I.
    • Journal Title

      Tetrahedron

      Volume: 72(48) Pages: 7866-7874

    • DOI

      10.1016/j.tet.2016.05.084

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydroalkylation of Alkenes Using Alkyl Iodides and Hantzch Ester under Palladium/Light System2016

    • Author(s)
      Sumino, S.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 18 Pages: 52-55

    • DOI

      10.1021/acs.orglett.5b03238

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photocatalytic One-Pot Synthesis of Homoallyl Ketones via a Norrish Type I Reaction of Cyclopentanones2015

    • Author(s)
      Okada,, M.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I.
    • Journal Title

      J. Org. Chem.

      Volume: 80 Pages: 9365-9369

    • DOI

      10.1021/acs.joc.5b01850

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photocatalyzed Site-Selective C-H to C-C Conversion of Aliphatic Nitriles2015

    • Author(s)
      Yamada, K.; Okada, M.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 17(5) Pages: 1292-1295

    • DOI

      10.1021/acs.orglett.5b00282

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] ynthesis of aromatic β-keto esters via a carbonylative Suzuki-Miyaura coupling reaction of α-iodo esters with arylboronic acids2015

    • Author(s)
      Sumino, S.; Ui. T.; Ryu, I.
    • Journal Title

      Org. Chem. Front.

      Volume: 2 Pages: 1085-1087

    • DOI

      10.1039/c5qo00185d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Carbonylative Mizoroki-Heck Reaction of Alkyl Iodides with Arylalkenes Using a Pd/Photoirradiation System2015

    • Author(s)
      Shuhei, S.; Ui, T.; Hamada, Y.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 17 Pages: 4952-4955

    • DOI

      10.1021/acs.orglett.5b02302

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids2015

    • Author(s)
      Furukawa, S.; Fukuyama, T.; Matsui, A.; Kuratsu, M.; Nakaya, R.; Ineyama, T.; Ueda, H.; Ryu, I.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Pages: 11980-11983

    • DOI

      10.1002/chem.201501783

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Carbonylative Couplings of Vinylogous Enolates: Application to Statin Structures2015

    • Author(s)
      Makarov, I. S.; Kuwahara, T.; Jusseau, X.; Ryu, I.; Lindhardt, A. T.; Skrydstrup, T.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Pages: 14043-14046

    • DOI

      10.1021/jacs.5b09342

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] cover Photoinduced Aminocarbonylation of Aryl Iodides2015

    • Author(s)
      Kawamoto, T.; Sato, A.; Ryu, I.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Pages: 14764-14767

    • DOI

      10.1002/chem.201503164

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones2014

    • Author(s)
      Okada, M.; Fukuyama, T.; Yamada, K.; Ryu, I.; Ravelli, D.; Fagnoni, M.
    • Journal Title

      Chem. Sci.

      Volume: 5(7) Pages: 2893-2898

    • DOI

      10.1039/c4sc01072h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Revisiting the bromination of C-H bonds with molecular bromine by using a photo-microflow system.2014

    • Author(s)
      Manabe, Y., Kitawaki, Y., Nagasaki, M., Fukase, K., Matsubara, H., Hino, Y., Fukuyama, T., Ryu, I.
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Pages: 12750-12753

    • DOI

      10.1002/chem.201402303

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Radical vinylation of dioxolanes and N-acylpyrrolidines using vinyl bromides2014

    • Author(s)
      Kippo, T.; Kimura, Y.; Maeda, A.; Matsubara, H.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Org. Chem. Front.

      Volume: 1 Pages: 755-758

    • DOI

      10.1039/c4qo00138a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Radical reactions of borohydrides2014

    • Author(s)
      Kawamoto, T.; Ryu, I.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 12(48) Pages: 9733-9742

    • DOI

      10.1039/c4ob01784f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A Theoretical Study on Reduction of Acyl Radicals with Borohydride Anions2014

    • Author(s)
      Kawamoto, T.; Matsubara, H.; Ryu, I.
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 7 Pages: 1140-1142

    • DOI

      10.1246/cl.140370

    • NAID

      130004868283

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Cyanoborohydride-Promoted Radical Arylation of Benzene2014

    • Author(s)
      Kawamoto, T. ; Sato, A. ; Ryu, I.
    • Journal Title

      Org. Lett.

      Volume: 16 Pages: 2111-2113

    • DOI

      10.1021/ol500614q

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A bromine-radical mediated three-component reaction comprising allenes, electron-deficient alkenes and allyl bromides: facile synthesis of 2-bromo-1,7-dienes2014

    • Author(s)
      Kippo, T.; Ryu, I.
    • Journal Title

      Chem. Commun.

      Volume: 50 Pages: 5993-5996

    • DOI

      10.1039/c4cc01597e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Recent Advances in Site-Selective C-H Functionalization by Radicals2018

    • Author(s)
      I. Ryu
    • Organizer
      三井化学触媒科学 seminar, 日本化学会 Festa, 2018.10.23 東京, 日本
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Recent Advances in Radical-Based Site-Selective C(sp3)-H Functionalization2018

    • Author(s)
      I. Ryu
    • Organizer
      The 13th International Symposium on Organic Reactions (ISOR-13), 2018.11.23.
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent Advances in Site-Selective C(sp3)-H Functionalization by Radicals,2018

    • Author(s)
      I. Ryu
    • Organizer
      EUCHEM Conference on Radical Reaction, Marseille, France, 2018.6.20.
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent Advances in Radical-Based Selective C(sp3)-H Functionalization2018

    • Author(s)
      I. Ryu
    • Organizer
      3rd International Symposium on Organic Chemistry GDUT, Guangzhou, China, November 8-9, 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent Advances in Radical-Based Site-Selective C(sp3)-H Functionalization2018

    • Author(s)
      I. Ryu
    • Organizer
      Mini-Symposium on Radical Chemistry in Organic Synthesis, University of Science and Technology of China October 12, 2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 原子移動型ラジカル反応を利用した極性官能基含有第二級アルキルホウ素化合物の合成2018

    • Author(s)
      森崎雄大、植田光洋、柳 日馨
    • Organizer
      第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 遷移金属触媒非存在下における分子内ヘックカルボニル化反応2018

    • Author(s)
      板東孝信・福山高英・柳日馨
    • Organizer
      第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Decatungstate光触媒を用いたエステル類の位置選択的C-Hアルキル化反応2018

    • Author(s)
      福山 高英・坂本 夏蓮・柳 日馨
    • Organizer
      第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] [2+2] Cycloadditions of 1,3-Bifunctional Allenes with C60 by using a Flow Reaction System2018

    • Author(s)
      橋下 拓幸、端山 美帆、棟近 愛子、植田 光洋、柳 日馨
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis(ICAMS-1)
    • Related Report
      2017 Annual Research Report
  • [Presentation] TBADT光触媒存在下、ピリジルアルカンの電子欠損オレフィンによる位置選択的なC-Hアルキル化反応2017

    • Author(s)
      西川 智大・山田 圭一・福山 高英・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] シリカゲル固定化3級アミン触媒を用いたシクロペンテン骨格を有するフラーレン誘導体のフロー合成2017

    • Author(s)
      端山 美帆・棟近 相衣子・植田 光洋・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒存在下、アントラニル酸のアルキンへのカルボアミノ化によるキノリノン類合成2017

    • Author(s)
      福山 高英・古川 拓宙・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒によるチオサリチル酸とアルキンからのチオクロメノン合成2017

    • Author(s)
      福山 高英・杉森 大樹・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒存在下、ビアリールカルボン酸とアルキンとの脱カルボニル化を伴った環化反応によるフェナントレン誘導体の合成2017

    • Author(s)
      福山 高英・坂手 拓哉・柳 日馨
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      kanagawa
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synergistic Polar/Steric Strategy in Achieving Site-Selective C(sp3)-H Functionalization of Cyclic Ketones and Lactones by Radicals2017

    • Author(s)
      Ilhyong Ryu
    • Organizer
      8th Pacific Symposium on Radical Chemistry, Australia
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photocatalyzed Site-Selective Functionalization of Pyridyl Alkanes2017

    • Author(s)
      Tomohiro Nshikawa, Keiichi Yamada, Takahide Fukuyama, Ilhyong Ryu
    • Organizer
      8th Pacific Symposium on Radical Chemistry, Australia
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A Synergistic Polar/Steric Strategy in Achieving Site-selective C(sp3)-H Functionalization by Radicals2017

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 1st National Symosium on Radical Chemistry, Soochow University, 中国
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cooperative Radical/Polar Annulation Approach to Nitrogen-Heterocycles2017

    • Author(s)
      Ilhyong Ryu
    • Organizer
      ISHC-26 ,Regensburg, Germany
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Potassium Substituted Halomethyltrifluoroborates by Atom-Transfer Radical Addition to Potassium Vinyltrifluoroborates2017

    • Author(s)
      森崎雄大、植田光洋、柳 日馨
    • Organizer
      The 11th International Symposium on Integrated Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] [2+2] Cycloadditions of 1,3-Bifunctional Allenes with C602017

    • Author(s)
      橋下 拓幸、端山 美帆、棟近 愛子、植田 光洋、柳 日馨
    • Organizer
      The 11th International Symposium on Integrated Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Non-Benzylic C(sp3 )-H Functionalization of Alkylpyridines Using TBADT as Photocatalyst2017

    • Author(s)
      Tomohiro Nshikawa, Keiichi Yamada, Takahide Fukuyama, Ilhyong Ryu
    • Organizer
      The 11th International Symposium on Integrated Synthesis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光レドックス触媒を用いたアルケン類の還元的ジフルオロアルキル化反応2017

    • Author(s)
      宇野 美沙恵, 隅野 修平, 福山 高英, 柳 日馨, 松浦 誠, 山本 明典, 岸川 洋介
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光触媒を用いたアルキルピリジンの位置選択的アルキル化反応2017

    • Author(s)
      西川 智大・山田 圭一・福山 高英・柳 日馨
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Site-selective Conversion of sp3 C-H Bond to C-C Bond by Photo-catalyst2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 10th International Symposium on Integrated Synthesis(ISONIS-10)
    • Place of Presentation
      Hyogo
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Palladium/Light Induced Vinylation of Iodoalkanes2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 12th International Symposium on Organic Free Radicals (ISOFR12)
    • Place of Presentation
      Shanghai
    • Year and Date
      2016-10-09
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent Advances in Flow Catalysis2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      14th International Conference on Micro Reaction Technology (IMRET14)
    • Place of Presentation
      Beijin
    • Year and Date
      2016-09-12
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Aryl Radical Carbonylation Induced by Photo-irradiation2016

    • Author(s)
      Ilhyong Ryu
    • Organizer
      The 12th International Symposium on Organic Reactions (ISOR-12)
    • Place of Presentation
      kyoto
    • Year and Date
      2016-04-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 極性効果と立体効果によって制御する位置選択的ラジカルC-H/C-C変換反応2016

    • Author(s)
      山田圭一, 福山高英, 柳 日馨
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Photocatalyzed C-H Arylation of Alkanes with Heterocycles2016

    • Author(s)
      藤井 沙紀・山田 圭一・福山 高英・柳 日馨
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Reductive Difluoromethylation of Unsaturated Hydrocarbons by Photoredox Catalyst2016

    • Author(s)
      隅野 修平・宇野 美沙恵・福山 高英・柳 日馨 松浦 誠・山本 明典・岸川 洋介
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Palladium/Light Combined System for Cross-coupling Reaction of Alkyl Iodides with Vinyl and Allyl Sulfones2016

    • Author(s)
      Shuhei SUMINO, Takahide FUKUYAMA, Ilhyong RYU
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Free Radical-Based Site-Selective C-H to C-C Conversion2015

    • Author(s)
      Ilhyong Ryu
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center, Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] The Use of Gas-Permeable PTFE Tube for Flow Carbonylation with ex-situ Generated Carbon Monoxide2015

    • Author(s)
      Ilhyong Ryu
    • Organizer
      21st ISFC & ISOFT’ 15
    • Place of Presentation
      Polytecnico di Milano; Como Campus, Como, Italy
    • Year and Date
      2015-08-23
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Novel C-C Bond Forming Reactions Induced by Photo-Irradiation2015

    • Author(s)
      Ilhyong Ryu
    • Organizer
      7th Pacific Symposium on Radical Chemistry (PSRC-7)
    • Place of Presentation
      Nanyang Technological University, Singapore
    • Year and Date
      2015-07-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Rhodium-Catalyzed Intermolecular Reaction of 1-Naphtoeic Acids with Internal Alkynes Leading to Perinaphthenones2015

    • Author(s)
      Takahide Fukuyama, Taiki Sugimori, Ilhyong Ryu
    • Organizer
      OMCOS
    • Place of Presentation
      Hotel Malia Sitges, Sitges-Barcelona, Spain
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Tricyclic Aromatics through Rh-Catalyzed Functionalization of Aromatic Carboxylic Acids2015

    • Author(s)
      Takahide Fukuyama
    • Organizer
      PRE-OMCOS Meeting
    • Place of Presentation
      ICIQ Audiorium, Tarragona, Spain
    • Year and Date
      2015-06-25
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ラジカル活性種の反応特性を基盤とする多成分系連結反応の開発2015

    • Author(s)
      柳 日馨
    • Organizer
      平成26年度有機合成化学協会賞受賞講演会
    • Place of Presentation
      如水会館(東京)
    • Year and Date
      2015-02-19
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Polycyclic Compounds thorugh Rhodium-catalyzed Cyclization of Aromaatic Carboxylic Acids2014

    • Author(s)
      Takahide Fukuyama
    • Organizer
      8th Singapore International Chemsitry Conference 2014
    • Place of Presentation
      National University of Singapore (Singapore)
    • Year and Date
      2014-12-15
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Recent Advances in Radical Carbonylations2014

    • Author(s)
      Ilhyong Ryu
    • Organizer
      Max Maracria Symposium
    • Place of Presentation
      Paris (France)
    • Year and Date
      2014-10-10
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Multicomponent Radical Reanctions2014

    • Author(s)
      Ilhyong Ryu
    • Organizer
      EUCHEM Conference on Organic Free Radicals
    • Place of Presentation
      Prague (Czech Republic)
    • Year and Date
      2014-07-02
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Book] 有機ラジカル反応の基礎2015

    • Author(s)
      柳 日馨
    • Total Pages
      156
    • Publisher
      丸善
    • Related Report
      2015 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2020-03-30  

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